N,N-Dimethylaniline → 2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-yl isobutyrate

HRID 1764048Notes

Reaction equation

[CH3:1][CH:2]1[CH2:6][CH2:5][C:4]2([C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH2:8][C:7]2([CH3:15])[OH:14])[O:3]1.CN(C)C1C=CC=CC=1.[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27]>>[C:25]([O:14][C:7]1([CH3:15])[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])([CH3:12])[C:4]21[O:3][CH:2]([CH3:1])[CH2:6][CH2:5]2)(=[O:29])[CH:26]([CH3:28])[CH3:27]

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 62325Isobutyryl chloride

HCID 6542853398-90-6

Product 1

HCID 233465722,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-yl isobutyrateYield 11%

Procedure

2.12 g (0.01 M) of 2,6,10,10-tetramethyl-1-oxa-spiro[4.5]decan-6-ol -- isomer A; see Example 1 -- were treated with a mixture of 12.1 g (0.1 M) of N,N-dimethylaniline and 5.3 g (0.05 M) pf isobutyryl chloride as indicated in Example 5 to give 0.3 g (ca. 11%) of the desired ester, b.p. 110°/0.5 Torr.

Sources & evidence

ORD record: ord-f79404b377df42c693c17d08e3711392
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04114630

Reaction notes

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