GB333313A - Improvements in and relating to the manufacture of aromatic oxyaldehydes - Google Patents

Improvements in and relating to the manufacture of aromatic oxyaldehydes

Info

Publication number
GB333313A
GB333313A GB1561829A GB1561829A GB333313A GB 333313 A GB333313 A GB 333313A GB 1561829 A GB1561829 A GB 1561829A GB 1561829 A GB1561829 A GB 1561829A GB 333313 A GB333313 A GB 333313A
Authority
GB
United Kingdom
Prior art keywords
vanillin
treated
propenyl
alkoxyvanillin
pyrocatechin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1561829A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell Riedel de Haen AG
Original Assignee
JD Riedel E de Haen AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JD Riedel E de Haen AG filed Critical JD Riedel E de Haen AG
Priority to GB1561829A priority Critical patent/GB333313A/en
Publication of GB333313A publication Critical patent/GB333313A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C07C47/58—Vanillin

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

333,313. Riedel-E. de HaÙn Akt.- Ges., J. D. May 18, 1929. Addition to 285,451 and 290,649. Vanillin; pyrocatecheuic aldchyde.-The mixture of alkoxyvanillin and 4-alkoxymethyl ether of 1-propenyl-3 : 4-pyrocatechin obtained by the alkaline oxidation with nitro compounds of the alkaline decomposition products of safrol, is separated by fractional acidification. The unoxidized propenyl compound, which is precipitated first, is alkylated, treated with dilute acids to remove the alkoxymethyl group and the resulting iseugenol or homologue oxidized to vanillin or its higher homologues. The alkoxyvanillin, after protection of the free hydroxy group, e.g. by acidylation, is treated first with dilute acids and then with alkylating agents so as to obtain vanillin or its homologues, the acidyl or other group being removed by saponification. Alternatively, the alkoxyvanillin is converted into protocatecheuic aldehyde by treatment with dilute acids. In one example, the oxidized products derived from safrol as described in Example 2 of Specification 290,649 are separated by addition of acetic acid. The 4-methoxymethylether of 1-propenyl-3 : 4- pyrocatechin dissolved in alcoholic caustic soda is treated with ethyl chloride and the ethylated product saponified with dilute acid in accordance with Specification 284,199 to obtain 1-propenyl- 3 : 4-pyrocatechin-3-ethylether. The latter is oxidized to the corresponding aldehyde by means of nitrobenzene. The methoxyvanillin separated by further addition of acetic acid is converted to protocatecheuic aldehyde by boiling a methyl alcoholic solution thereof with mineral acid. In a second example, the methoxyvanillin is treated with benzenesulphonyl chloride to protect the hydroxy group, and the methoxymethyl group removed by boiling with a little hydrochloric acid in methyl alcoholic solution. After methylation with dimethylsulphate the resulting benzene sulphonic ester of vanillin is saponified with alcoholic caustic soda to give vanillin. Specifications 285,551 and 318,939 also are referred to.
GB1561829A 1929-05-18 1929-05-18 Improvements in and relating to the manufacture of aromatic oxyaldehydes Expired GB333313A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1561829A GB333313A (en) 1929-05-18 1929-05-18 Improvements in and relating to the manufacture of aromatic oxyaldehydes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1561829A GB333313A (en) 1929-05-18 1929-05-18 Improvements in and relating to the manufacture of aromatic oxyaldehydes

Publications (1)

Publication Number Publication Date
GB333313A true GB333313A (en) 1930-08-14

Family

ID=10062389

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1561829A Expired GB333313A (en) 1929-05-18 1929-05-18 Improvements in and relating to the manufacture of aromatic oxyaldehydes

Country Status (1)

Country Link
GB (1) GB333313A (en)

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